feat(jira): add optional roadmap-based labeling for synced issues

Added `labelRoadmapSource` config option to automatically label Jira issues with sanitized roadmap titles. Implemented `sanitizeRoadmapLabel`, `addLabelToIssue`, and `applyRoadmapLabel` helpers to create lowercase-hyphenated labels from roadmap names. Updated `syncMilestone`, `syncInitiative`, `syncWorkflow`, and `syncPulses` to accept optional `roadmapTitle` parameter and apply labels after issue creation/update. Modified JiraSyncQueue to fetch

Author: wgraham17

src/backend/services/jira.ts

@@ -829,11 +829,51 @@ async function findIssueTypeId(
 	return match?.id ?? null;
 }
 
+// =============================================================================
+// Roadmap Labeling
+// =============================================================================
+
+function sanitizeRoadmapLabel(title: string): string {
+	return title
+		.toLowerCase()
+		.replace(/[^a-z0-9]+/g, "-")
+		.replace(/^-|-$/g, "");
+}
+
+async function addLabelToIssue(
+	auth: JiraAuth,
+	issueKey: string,
+	label: string,
+): Promise<boolean> {
+	const result = await jiraFetch(auth, "PUT", `/issue/${issueKey}`, {
+		update: { labels: [{ add: label }] },
+	});
+	return result.ok;
+}
+
+async function applyRoadmapLabel(
+	auth: JiraAuth,
+	config: JiraConfig,
+	issueKey: string,
+	roadmapTitle: string | undefined,
+): Promise<void> {
+	if (!config.labelRoadmapSource || !roadmapTitle) return;
+	const label = sanitizeRoadmapLabel(roadmapTitle);
+	if (!label) return;
+	const ok = await addLabelToIssue(auth, issueKey, label);
+	if (!ok) {
+		log.jira.warn(`Failed to apply roadmap label "${label}" to ${issueKey}`);
+	}
+}
+
 /**
  * Sync a Milestone → Jira Epic
  * Creates or updates the Epic in Jira.
  */
-export async function syncMilestone(milestone: Milestone): Promise<void> {
+export async function syncMilestone(
+	milestone: Milestone,
+	roadmapTitle?: string,
+): Promise<void> {
 	const ctx = await resolveConfigAndAuth();
 	if (!ctx?.config.syncRoadmaps) return;
 
@@ -842,9 +882,10 @@ export async function syncMilestone(milestone: Milestone): Promise<void> {
 	await updateMilestoneSyncStatus(milestone.id, "pending");
 
 	try {
-		if (milestone.jiraEpicKey) {
+		const existingEpicKey = milestone.jiraEpicKey;
+		if (existingEpicKey) {
 			// Update existing
-			const success = await updateIssue(auth, milestone.jiraEpicKey, {
+			const success = await updateIssue(auth, existingEpicKey, {
 				summary: milestone.title,
 				...(milestone.description
 					? {
@@ -855,8 +896,9 @@ export async function syncMilestone(milestone: Milestone): Promise<void> {
 
 			if (success) {
 				await updateMilestoneSyncStatus(milestone.id, "synced");
+				await applyRoadmapLabel(auth, config, existingEpicKey, roadmapTitle);
 				log.jira.info(
-					`Updated Epic ${milestone.jiraEpicKey} for milestone ${milestone.id}`,
+					`Updated Epic ${existingEpicKey} for milestone ${milestone.id}`,
 				);
 			} else {
 				await updateMilestoneSyncStatus(
@@ -900,6 +942,7 @@ export async function syncMilestone(milestone: Milestone): Promise<void> {
 					issue.key,
 					issue.id,
 				);
+				await applyRoadmapLabel(auth, config, issue.key, roadmapTitle);
 				log.jira.info(
 					`Created Epic ${issue.key} for milestone ${milestone.id}`,
 				);
@@ -933,6 +976,7 @@ export async function syncMilestone(milestone: Milestone): Promise<void> {
 export async function syncInitiative(
 	initiative: Initiative,
 	parentEpicKey?: string,
+	roadmapTitle?: string,
 ): Promise<void> {
 	const ctx = await resolveConfigAndAuth();
 	if (!ctx?.config.syncRoadmaps) return;
@@ -945,7 +989,8 @@ export async function syncInitiative(
 		config.initiativePriorityMapping[initiative.priority] ?? undefined;
 
 	try {
-		if (initiative.jiraIssueKey) {
+		const existingIssueKey = initiative.jiraIssueKey;
+		if (existingIssueKey) {
 			// Update existing
 			const fields: Record<string, unknown> = {
 				summary: initiative.title,
@@ -957,12 +1002,13 @@ export async function syncInitiative(
 				fields.priority = { id: priorityId };
 			}
 
-			const success = await updateIssue(auth, initiative.jiraIssueKey, fields);
+			const success = await updateIssue(auth, existingIssueKey, fields);
 
 			if (success) {
 				await updateInitiativeSyncStatus(initiative.id, "synced");
+				await applyRoadmapLabel(auth, config, existingIssueKey, roadmapTitle);
 				log.jira.info(
-					`Updated Story ${initiative.jiraIssueKey} for initiative ${initiative.id}`,
+					`Updated Story ${existingIssueKey} for initiative ${initiative.id}`,
 				);
 			} else {
 				await updateInitiativeSyncStatus(
@@ -1008,6 +1054,7 @@ export async function syncInitiative(
 					issue.key,
 					issue.id,
 				);
+				await applyRoadmapLabel(auth, config, issue.key, roadmapTitle);
 				log.jira.info(
 					`Created Story ${issue.key} for initiative ${initiative.id}`,
 				);
@@ -1043,6 +1090,7 @@ export async function syncInitiative(
 export async function syncWorkflow(
 	workflow: Workflow,
 	initiativeJira?: { key: string; id?: string },
+	roadmapTitle?: string,
 ): Promise<void> {
 	const ctx = await resolveConfigAndAuth();
 	if (!ctx?.config.syncWorkflows) return;
@@ -1072,6 +1120,8 @@ export async function syncWorkflow(
 			} else {
 				await updateWorkflowSyncStatus(workflow.id, "synced");
 			}
+			// Label the adopted issue (idempotent if initiative sync already labelled it)
+			await applyRoadmapLabel(auth, config, initiativeJira.key, roadmapTitle);
 		} else if (workflow.jiraIssueKey) {
 			// Standalone workflow — update existing Story
 			const fields: Record<string, unknown> = {
@@ -1343,6 +1393,7 @@ export async function syncArtifactComment(
 export async function syncPulses(
 	plan: Plan,
 	parentTaskKey: string,
+	roadmapTitle?: string,
 ): Promise<void> {
 	const ctx = await resolveConfigAndAuth();
 	if (!ctx?.config.syncWorkflows) return;
@@ -1401,6 +1452,8 @@ export async function syncPulses(
 					await repos.pulses.updateJiraIssueId(existingPulse.id, issue.key);
 				}
 
+				await applyRoadmapLabel(auth, config, issue.key, roadmapTitle);
+
 				// Assign sub-task to the authenticated user
 				try {
 					const accountId = await getCurrentUserAccountId(auth);

src/backend/services/jiraSyncQueue.ts

@@ -162,7 +162,10 @@ class JiraSyncQueue {
 				const initiativeJira = initiative?.jiraIssueKey
 					? { key: initiative.jiraIssueKey, id: initiative.jiraIssueId }
 					: undefined;
-				await syncWorkflow(workflow, initiativeJira);
+				const roadmap = initiative?.roadmapId
+					? await repos.roadmaps.getRoadmap(initiative.roadmapId)
+					: null;
+				await syncWorkflow(workflow, initiativeJira, roadmap?.title);
 
 				return;
 			}
@@ -226,7 +229,8 @@ class JiraSyncQueue {
 					);
 					return;
 				}
-				await syncMilestone(milestone);
+				const roadmap = await repos.roadmaps.getRoadmap(milestone.roadmapId);
+				await syncMilestone(milestone, roadmap?.title);
 				return;
 			}
 
@@ -243,7 +247,12 @@ class JiraSyncQueue {
 				const milestone = await repos.roadmaps.getMilestone(
 					initiative.milestoneId,
 				);
-				await syncInitiative(initiative, milestone?.jiraEpicKey);
+				const roadmap = await repos.roadmaps.getRoadmap(initiative.roadmapId);
+				await syncInitiative(
+					initiative,
+					milestone?.jiraEpicKey,
+					roadmap?.title,
+				);
 				return;
 			}
 
@@ -263,7 +272,13 @@ class JiraSyncQueue {
 					return;
 				}
 
-				await syncPulses(plan, workflow.jiraIssueKey);
+				const initiative = await repos.roadmaps.findInitiativeByWorkflowId(
+					job.workflowId,
+				);
+				const roadmap = initiative?.roadmapId
+					? await repos.roadmaps.getRoadmap(initiative.roadmapId)
+					: null;
+				await syncPulses(plan, workflow.jiraIssueKey, roadmap?.title);
 				return;
 			}
 

src/features/settings/components/JiraSection.tsx

@@ -8,6 +8,7 @@ import {
 } from "lucide-react";
 import { useCallback, useEffect, useState } from "react";
 import { Button } from "@/components/ui/button";
+import { Checkbox } from "@/components/ui/checkbox";
 import { Input } from "@/components/ui/input";
 import {
 	Select,
@@ -554,6 +555,37 @@ export function JiraSection() {
 				</div>
 			)}
 
+			{/* Roadmap label toggle */}
+			{credentialsConfigured && config && !isEditing && (
+				<div className="mt-3 flex items-start gap-2">
+					<Checkbox
+						id="jira-label-roadmap"
+						checked={config.labelRoadmapSource}
+						onCheckedChange={async (checked) => {
+							const updated: JiraConfig = {
+								...config,
+								labelRoadmapSource: checked === true,
+							};
+							setConfig(updated);
+							await saveJiraConfig(updated);
+						}}
+						className="mt-0.5"
+					/>
+					<label
+						htmlFor="jira-label-roadmap"
+						className="text-xs text-zinc-400 cursor-pointer select-none"
+					>
+						<span className="text-zinc-300">
+							Label issues with roadmap name
+						</span>
+						<br />
+						Adds a sanitized label (e.g.{" "}
+						<code className="text-zinc-500">observability-and-monitoring</code>)
+						to every Jira issue created from a roadmap.
+					</label>
+				</div>
+			)}
+
 			{/* Status & Priority Mapping Panel */}
 			{credentialsConfigured && config && !isEditing && (
 				<div className="mt-3">

src/shared/schemas/jira.ts

@@ -47,6 +47,9 @@ export const JiraConfigSchema = z.object({
 	syncWorkflows: z.boolean().default(true),
 	syncArtifacts: z.boolean().default(true),
 
+	// Labeling
+	labelRoadmapSource: z.boolean().default(false),
+
 	// Status mapping per Autarch object type
 	statusMapping: z
 		.object({